Ryan Frawley
Some weather we’re having, huh?
Look, there’s nothing wrong with small talk. Nothing lubes the wheels of social interaction like some inoffensive chatter.
But if you really want to get to know someone better, or you want to explore deeper topics, you need to get beyond the formalities.
It’s not always easy to spark a deep conversation. But there are some ways you can get past small talk and into some more stimulating conversations.
Best of all, sparking a deep conversation could be as simple as asking the right questions.
Next time you want to take the conversation to the next level, try some of these questions to encourage a seriously deep talk.
1) If you had infinite money, how would you spend your time?
This is a fantastic question to ask anyone.
So much of what we do is for money. Often, even people who really enjoy their jobs would do something different if they didn’t need the paycheck.
This is a great question to spark a deep conversation because the answer requires people to tell you what they are most passionate about.
Let’s face it. People are never more interesting than when they are talking about what they love, so getting someone to tell you about their passions is a wonderful way to get to know more about them as a person.
And there’s more.
This is also a great question to ask yourself from time to time. You’ll never have infinite money, but how close is your life to the way you want it to be?
And if you’re a long way away from everything you want, maybe it’s time you started working on that.
2) What’s one thing you would change about yourself if you could?
This can be a tough question to answer. It requires a certain level of emotional honesty that can be hard to achieve with a stranger.
That makes this a question better asked of someone you already know fairly well. It’s also a question you may want to avoid if you’re talking to someone with low self-esteem.
On the other hand, people with a strong personality who are able to be critical of themselves can come up with some amazing answers to a question like this.
Even better, you’ll learn a lot about anyone you ask this question of. Not just their insecurities, but also their hopes and their dreams.
3) What’s the hardest thing you’ve ever done?
Once, when I was working a boring job ripping tickets at the movie theater, a coworker asked me this question, more or less out of the blue.
It really got me thinking.
In many ways, our hardships and tribulations define us. They make us who we are. So asking someone about the hardest thing they’ve been through tells you a lot about who they are.
My answer back then was that I moved away from everyone and everything I knew when I was twenty to live in a foreign country where I had never been before.
That might still be my answer now, and I think it reveals something about my personality.
Plus, like any question designed to spark a deep conversation, it leaves lots of room for follow-up questions. For instance, in my case, why did you do it?
But that’s a story for another day…
4) What have you gained from your current job besides money?
There’s nothing wrong with taking a job for money. Not many of us get to do exactly what we want and get paid for it at the same time.
On the other hand, every job has something to teach you, even if it is just ripping tickets in a movie theater. Jobs can give us a lot, whether it’s new friends, useful skills, or just life lessons.
You see, even a job you hate can teach you something valuable about what you want in life and what you don’t want.
Most people have jobs, so this is an excellent question to ask just about anyone.
5) What’s the most valuable lesson your parents taught you?
Everyone has parents, even if they’re not around anymore. And even bad parents can teach their children something.
This can be quite a personal question to ask someone, so it might be better used on people you know fairly well already.
With that said, it can quickly get you into a deep conversation, since it forces you to think about the way the experiences you received in childhood continue to shape your life to this day.
This can be a heavy conversation, but there’s no denying this question can lead to rewardingly deep discussions.
6) If you could live anywhere, where would it be and why?
This is a fun one. It gets people to tell you about the places they love, whether they’ve ever been there or not.
Even better, it leaves lots of room for follow-up questions.
If I was asked this question, my answer would probably be Italy. Except I can live in Italy. I used to. But I don’t anymore. Why not? Why don’t I live in a place that I enjoy so much?
The answers to those questions lead into various stories that reveal a lot about me. A deep conversation is almost guaranteed from this question.
7) Do you believe in karma? Why or why not?
This is a great one.
Karma means lots of different things to different people.
It’s an important religious concept in Asian religions like Buddhism and Hinduism, but it’s also well known in the West, where it is often seen as a kind of cosmic balance that happens in this life rather than affecting reincarnation in the next.
This is a good question to ask to start a deep conversation, because no matter what the person answers, you can follow up with more questions to determine what they believe in.
Whether they believe that every action we can possibly take its predetermined down to the last detail, or they believe that all existence is random chaos, this question sparks some deep philosophical conversations.
8) Who do you wish you were more like?
This is another great question to ask someone you want to get to know better.
A person’s heroes tell you a lot about them and what they aspire to be.
You can keep the question open-ended so they can answer with someone they know personally, like a parent, or a celebrity they admire.
And there’s more.
This is another open-ended question that allows plenty of follow-ups, so you can learn more about the way a person wants to be. There aren’t many better ways to get to know someone better than that.
9) What are three things you can’t live without?
Just three things. That’s the rule. Anyone you ask it has to think carefully about their response.
As if that’s not enough, this question is also open enough that people can choose to answer in a number of ways.
They can be silly and humorous about it, or give you an answer that’s much deeper and more heartfelt. That makes this a great question to introduce into any conversation you want to take a little deeper.
It also tells you what value they place on different things in their life.
No wonder this is a popular question to ask anyone you want to get to know a bit better.
10) What you think is the best time in history to be alive?
Ask a history buff this question, and you may be in for an hour-long lecture.
On the other hand, people don’t have to know much about history can still have an idea how they would answer.
And the answer they give can tell you a lot about their understanding of the past, as well as what they consider makes a good life.
Personally, my answer is a little boring: now.
Even if the news we hear makes it seem otherwise, I don’t believe the world has ever been better than it is right now.
There’s less poverty, greater quality, and greater opportunities for personal growth now than at any other time in human history.
Plus, we can order tacos online.
But everyone has a different answer to this question.
And however they answer, you’re in for deep conversation as you ponder what makes life worth living.
11) If you could live in a completely convincing virtual reality, would you?
By now, you’ve probably noticed that the best deep questions are those that allow open-ended answers and further exploration of the topic.
This final question is definitely one of those.
And as technology advances and AI and virtual reality become ever more powerful, this may well be a question we all have to ask ourselves in the future.
We all saw those Matrix films. Would you like to live in a blissful utopia where everything is perfect and nothing is real?
Or would you rather live in the real world, with all its problems, its suffering, and its compromises?
A question like this just begs anyone you ask it to think carefully about what they value in life. No wonder it leads to such deep conversations.
Starting a deep conversation is easy
If you’re tired of talking about the weather or your local sports team, give some of these deep topics a go. Questions like these that go deep are the perfect way to get to know someone better.
And who knows?
You may even find your own views changing as you explore these deep topics with other people.
